JP4352103B2 - 1,3−ジ飽和−2−不飽和トリグリセリドの分別方法 - Google Patents
1,3−ジ飽和−2−不飽和トリグリセリドの分別方法 Download PDFInfo
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- JP4352103B2 JP4352103B2 JP2009509804A JP2009509804A JP4352103B2 JP 4352103 B2 JP4352103 B2 JP 4352103B2 JP 2009509804 A JP2009509804 A JP 2009509804A JP 2009509804 A JP2009509804 A JP 2009509804A JP 4352103 B2 JP4352103 B2 JP 4352103B2
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- fatty acid
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- triglyceride
- oils
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- 150000003626 triacylglycerols Chemical class 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 40
- 239000003921 oil Substances 0.000 claims description 144
- 239000003925 fat Substances 0.000 claims description 129
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 89
- 229930195729 fatty acid Natural products 0.000 claims description 89
- 239000000194 fatty acid Substances 0.000 claims description 89
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 79
- 239000007788 liquid Substances 0.000 claims description 78
- 150000004671 saturated fatty acids Chemical group 0.000 claims description 59
- 239000007787 solid Substances 0.000 claims description 50
- 125000005907 alkyl ester group Chemical group 0.000 claims description 46
- 150000004665 fatty acids Chemical class 0.000 claims description 45
- 238000001914 filtration Methods 0.000 claims description 41
- 238000004821 distillation Methods 0.000 claims description 40
- 238000000926 separation method Methods 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 238000002425 crystallisation Methods 0.000 claims description 23
- 230000008025 crystallization Effects 0.000 claims description 23
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
- 238000003825 pressing Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000005194 fractionation Methods 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- 235000014593 oils and fats Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 description 121
- 235000019197 fats Nutrition 0.000 description 109
- 239000000203 mixture Substances 0.000 description 52
- 239000004367 Lipase Substances 0.000 description 41
- 102000004882 Lipase Human genes 0.000 description 41
- 108090001060 Lipase Proteins 0.000 description 41
- 235000019421 lipase Nutrition 0.000 description 41
- 229940040461 lipase Drugs 0.000 description 40
- 239000000843 powder Substances 0.000 description 36
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 28
- 244000299461 Theobroma cacao Species 0.000 description 24
- 235000014121 butter Nutrition 0.000 description 24
- 239000000306 component Substances 0.000 description 24
- 235000019219 chocolate Nutrition 0.000 description 21
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 21
- 239000002994 raw material Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 235000010469 Glycine max Nutrition 0.000 description 13
- 244000068988 Glycine max Species 0.000 description 13
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical group CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 238000011085 pressure filtration Methods 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 9
- 238000001256 steam distillation Methods 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 7
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940110456 cocoa butter Drugs 0.000 description 6
- 235000019868 cocoa butter Nutrition 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 6
- 235000019482 Palm oil Nutrition 0.000 description 5
- 235000019486 Sunflower oil Nutrition 0.000 description 5
- 229940067592 ethyl palmitate Drugs 0.000 description 5
- 239000002540 palm oil Substances 0.000 description 5
- 239000002600 sunflower oil Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- -1 for example Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 3
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 3
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 235000001046 cacaotero Nutrition 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 241000282693 Cercopithecidae Species 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 241000303962 Rhizopus delemar Species 0.000 description 2
- 240000005384 Rhizopus oryzae Species 0.000 description 2
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003910 behenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FDCOHGHEADZEGF-QPLCGJKRSA-N 1,3-dipalmitoyl-2-oleoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC FDCOHGHEADZEGF-QPLCGJKRSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 235000005956 Cosmos caudatus Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241001522296 Erithacus rubecula Species 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- BCQDFMKSIQCOGR-QYIMKBBWSA-N TG(18:0/18:2(9Z,12Z)/18:0) Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCCCCCCCCCCCC BCQDFMKSIQCOGR-QYIMKBBWSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000012533 medium component Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000013322 soy milk Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0075—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007232567 | 2007-09-07 | ||
JP2007232567 | 2007-09-07 | ||
JP2008053465 | 2008-03-04 | ||
JP2008053465 | 2008-03-04 | ||
PCT/JP2008/066173 WO2009031680A1 (ja) | 2007-09-07 | 2008-09-08 | 1,3-ジ飽和-2-不飽和トリグリセリドの分別方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP4352103B2 true JP4352103B2 (ja) | 2009-10-28 |
JPWO2009031680A1 JPWO2009031680A1 (ja) | 2010-12-16 |
Family
ID=40428991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009509804A Active JP4352103B2 (ja) | 2007-09-07 | 2008-09-08 | 1,3−ジ飽和−2−不飽和トリグリセリドの分別方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US8389754B2 (de) |
EP (4) | EP2388307A1 (de) |
JP (1) | JP4352103B2 (de) |
KR (1) | KR101010572B1 (de) |
CN (1) | CN101848981B (de) |
DK (3) | DK2213712T3 (de) |
ES (3) | ES2437849T3 (de) |
MY (1) | MY147857A (de) |
RU (1) | RU2431654C1 (de) |
TW (1) | TWI441915B (de) |
WO (1) | WO2009031680A1 (de) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010209147A (ja) * | 2009-03-06 | 2010-09-24 | Nisshin Oillio Group Ltd | 油脂の製造方法 |
JP2010209153A (ja) * | 2009-03-06 | 2010-09-24 | Nisshin Oillio Group Ltd | 油脂の製造方法 |
US11147285B2 (en) | 2015-09-24 | 2021-10-19 | The Nisshin Oillio Group, Ltd. | Powdery fat or oil composition and method for producing same |
US11219224B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
US11220654B2 (en) * | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11241020B2 (en) | 2016-01-21 | 2022-02-08 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11246322B2 (en) | 2016-01-21 | 2022-02-15 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
US11292989B2 (en) | 2014-07-22 | 2022-04-05 | The Nisshin Oillio Group, Ltd. | Powdered fat/oil composition, food including powdered fat/oil composition, and methods for producing same |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4826848B2 (ja) * | 2009-03-30 | 2011-11-30 | 不二製油株式会社 | サル脂分別油の製造法 |
PL2251428T3 (pl) * | 2009-05-11 | 2012-05-31 | Loders Croklaan Bv | Sposób wytwarzania kompozycji triglicerydowej |
CN102802429B (zh) * | 2010-03-19 | 2014-07-09 | 日清奥利友集团株式会社 | 油脂组合物及使用该油脂组合物的巧克力制品 |
EP2561765A4 (de) * | 2010-04-22 | 2017-05-10 | CJ CheilJedang Corporation | Trockenfraktionierungsverfahren für eine transveresterte öl- und fettzusammensetzung |
KR101314682B1 (ko) * | 2010-04-22 | 2013-10-07 | 씨제이제일제당 (주) | 카카오 버터 유사 하드버터의 제조 방법 |
WO2011158909A1 (ja) * | 2010-06-18 | 2011-12-22 | 日清オイリオグループ株式会社 | 起泡性水中油型乳化物用油脂組成物および該油脂組成物を含んでなる起泡性水中油型乳化物 |
MY161610A (en) * | 2010-09-27 | 2017-04-28 | Nisshin Oillio Group Ltd | Oil and fat composition and method of producing thereof |
CN102958374B (zh) * | 2011-01-31 | 2014-05-28 | 日清奥利友集团株式会社 | 棕榈分提软质油及使用该棕榈分提软质油的加工乳化食品 |
WO2012169457A1 (ja) * | 2011-06-06 | 2012-12-13 | 日清オイリオグループ株式会社 | 油脂の分別方法 |
MY169820A (en) * | 2011-09-09 | 2019-05-16 | Sime Darby Plantation Berhad | A method for producing triacylglycerol oil |
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Cited By (8)
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JP2010209147A (ja) * | 2009-03-06 | 2010-09-24 | Nisshin Oillio Group Ltd | 油脂の製造方法 |
JP2010209153A (ja) * | 2009-03-06 | 2010-09-24 | Nisshin Oillio Group Ltd | 油脂の製造方法 |
US11292989B2 (en) | 2014-07-22 | 2022-04-05 | The Nisshin Oillio Group, Ltd. | Powdered fat/oil composition, food including powdered fat/oil composition, and methods for producing same |
US11147285B2 (en) | 2015-09-24 | 2021-10-19 | The Nisshin Oillio Group, Ltd. | Powdery fat or oil composition and method for producing same |
US11219224B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
US11220654B2 (en) * | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11241020B2 (en) | 2016-01-21 | 2022-02-08 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11246322B2 (en) | 2016-01-21 | 2022-02-15 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
Also Published As
Publication number | Publication date |
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DK2213712T3 (da) | 2014-01-20 |
ES2438170T3 (es) | 2014-01-16 |
EP2399977B1 (de) | 2013-11-27 |
JPWO2009031680A1 (ja) | 2010-12-16 |
EP2388306A1 (de) | 2011-11-23 |
ES2437927T3 (es) | 2014-01-15 |
EP2399977A1 (de) | 2011-12-28 |
RU2431654C1 (ru) | 2011-10-20 |
TW200920840A (en) | 2009-05-16 |
EP2388306B1 (de) | 2013-11-27 |
ES2437849T3 (es) | 2014-01-14 |
US8389754B2 (en) | 2013-03-05 |
MY147857A (en) | 2013-01-31 |
EP2388307A1 (de) | 2011-11-23 |
DK2399977T3 (en) | 2014-02-24 |
US20100222607A1 (en) | 2010-09-02 |
DK2388306T3 (en) | 2014-02-24 |
CN101848981B (zh) | 2014-06-11 |
KR20100043111A (ko) | 2010-04-27 |
CN101848981A (zh) | 2010-09-29 |
EP2213712A1 (de) | 2010-08-04 |
TWI441915B (zh) | 2014-06-21 |
EP2213712B1 (de) | 2013-11-27 |
EP2213712A4 (de) | 2012-02-22 |
WO2009031680A1 (ja) | 2009-03-12 |
KR101010572B1 (ko) | 2011-01-24 |
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